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<h1><a href="https://archiveofourown.org/works/29654130">Teasing Dean</a> by <a class='authorlink' href='https://archiveofourown.org/users/Felurian1/pseuds/Felurian1'>Felurian1</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Aftercare, Anal Fingering, Control, Dom Castiel/Sub Dean Winchester, M/M, Orgasm Delay/Denial, Punishment, Roleplay, Spanking, Student Dean Winchester, Teacher Castiel (Supernatural), Teacher/Student Roleplay, Teasing</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2021-02-23</td></tr>

<tr><td><b>Updated:</b></td><td>2021-02-23</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-15 21:53:34</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,925</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/29654130</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Felurian1/pseuds/Felurian1</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean's been trying to get Mr Novak's attention, and now it's finally worked. But Castiel has something a little less traditional in mind for Dean's discipline today. After all, the punishment should fit the crime, no?</p><p>(This is a fully discussed roleplay scene with aftercare)</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>111</td></tr>

</table>

<a name="section0001"><h2>Teasing Dean</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Dean knows he’s in trouble, waiting outside Mr Novak’s office for him to call him in. He’s been acting up deliberately, pushing the boundaries to see where it would get him. Wearing his gym shorts lower and tighter, removing the white vest he normally wears beneath his shirt to let just a hint of his nipples show through. And then today, the ultimate risk, coming to class with no underwear, just the tantalising rub of his pants keeping him on edge all day. And now this. Dean has been watching Castiel since he arrived at the start of term, drawn to the authority in his voice, though he’d never admit to that. </p><p>He stands outside the principal’s door, uncomfortably aware of the slight wetness in his pants in anticipation of what’s happening next.</p><p>“Come in, Dean.”</p><p>He nervously opens the door and walks into Mr Novak’s study. It’s as Dean expected, heavy furniture left over from the previous occupant, books strewn across the desk. He turns his attention to Castiel, and sees his expression is stern. Dean swallows, and feels himself shiver in fear and desire for him, for his attention.</p><p>“Dean, this has to stop. I’ve had several reports of you in inappropriate uniform, from a number of teachers. What’s made you act like this?”</p><p>Dean hesitates, shakes his head slightly.</p><p>“I don’t know if it’s some kind of plea for attention, but I can’t let it slide. You know we have a code of conduct here,” and Dean nods in response to that, “and if this continues I’ll have to inform your sponsor. I should have done so already.”</p><p>Dean’s pulse quickens as he contemplates that, how ashamed he’d be to have to explain himself.</p><p>“Please, sir, don’t do that. I’ll… I’ll do detention or something!”</p><p>Dean sees Mr Novak smile, as though he’d been expecting that response.</p><p>“I’m a big believer in the punishment fitting the crime. It makes sense to me, don’t you agree?”</p><p>Dean nods, confused, as Castiel continues.</p><p>“You’ve been being very provocative, very naughty. And I’m not sure detention is really the right response. After all, I have a duty to make sure you finish this school as a polite, well behaved young man, don’t I?”</p><p>“Yes sir, but--”</p><p>“No, no buts Dean. I think I should tell your sponsor about this after all…. Unless you’re willing to accept a suitable punishment.”</p><p>“Yes sir please, just don’t tell anyone?” Dean says, pleadingly.</p><p>Something seems to change in Castiel, as though Dean said just the right thing, as though he was waiting for him to say it. He smiles at Dean, properly this time.</p><p>“Alright. I’ll give you a chance. Go and stand by the desk over there, and put both your hands on it. I want to see a straight back, straight legs shoulder width apart okay?”</p><p>Shaking, Dean does as he says, obediently walking to the desk and placing both hands on it, then backing up a few steps to stretch out his back. </p><p>“I need your pants off please Dean”, Mr Novak says, and Dean hurries to obey, blushing furiously as he realises that Castiel will be able to see everything. He’ll know Dean didn’t wear underwear today. </p><p>Dean only hesitates for a moment though before making his decision, unbuckling his belt and letting his pants slide to the floor. He straightens up a little, only to feel Mr Novak’s hand on his shoulder, pushing him back down into place. Castiel walks behind him, and Dean knows he must be considering his position.</p><p>“Legs a little wider please”, comes the calm instruction.</p><p>Dean flushes again, and inches his feet apart a little further, feeling the air against his exposed hole. His cock is starting to fill out nicely, the anticipation of whatever Castiel is about to do making him hard and aching. He looks straight ahead, determined to see this through. And maybe get a little extra besides. He hasn’t been dressing like this for nothing, after all.</p><p>Dean is shocked out of his thoughts by a sharp stinging pain as without warning Castiel’s hand makes contact with his raised ass. He yelps in pain and surprise, twisting his head to see the teacher, but he stays just out of Dean’s line of sight.</p><p>“I was going to use my ruler, but since you have prepared yourself to be spanked already, I will take the more traditional approach,” Castiel says, his tone reassuring but firm. “This will hurt, but not for too long. Just enough to make the lesson memorable.”</p><p>Before Dean has time to form a reply, Cas’s hand lands again, a loud snapping noise filling the air and jolting him forwards onto his hands. He loses track of time as he’s spanked again and again, Castiel’s relentless strokes punctuated only by brief pauses when Dean loses his positioning. Eventually he stops, and Dean gasps, trying to catch his breath.</p><p>“There now, that wasn’t so bad was it? You have turned a lovely shade of pink, Dean.”</p><p>Dean squirms, aware that he can’t hide from Mr Novak’s gaze while he stays like this.</p><p>“You even seem to have been… enjoying yourself?”</p><p>Dean whines quietly as he feels one finger lightly trace the length of his cock, making him feel how hard and slick he is now. He hadn’t felt it happen, but he suddenly realises he must have been dripping onto the floor, and a low moan escapes his mouth. The finger disappears, as Castiel seems to be considering something.</p><p>“Sir? Can I… Can I move now?”</p><p>Dean feels rather than sees Cas shake his head.</p><p>“No I don’t think so Dean. I would have left it there but this reaction from you indicates a deeper sluttishness than I had anticipated. It must be dealt with before we are finished here, do you understand?”</p><p>“I… yes, sir,” Dean says, feeling more wetness spilling from his cock as he accepts it. He hears the sound of a bottle cap being opened, and then a sticky sound as Castiel continues to talk.</p><p>“Good. Now, I am going to place my fingers inside you Dean, and use them to make you… excited. Under no circumstances may you give in to these sensations, do you understand?”</p><p>Cas doesn’t wait for his response as he places one hand on Dean’s ass, keeping him still, and slowly inserts a single slick finger into his ass. The feeling is incredible, he knows this is what he’s been waiting for ever since Mr Novak arrived, and he tries to keep still, shuffling his legs further apart reflexively.</p><p>“Good, yes that’s good, you’re doing well. You’re very tight here Dean, so I’m only going to give you three fingers today, okay? I promise it won’t hurt, but you might feel a little stretched.”</p><p>Dean nods, incapable of speaking as Castiel starts to move his finger. He thought it would hurt but this feeling is perfect, the stretch and the friction driving him wild. He feels a second finger nudging against his hole, and then a deeper stretch, burning just a little this time, as Castiel’s second finger slowly and gently pushes inside him too.</p><p>Castiel allows him a moment to adjust to the new tightness, then slowly begins to withdraw the fingers from his ass, making him moan with displeasure. Castiel laughs softly, and the fingers move deeper again, in and out, heat building deep in Dean’s belly as his cock hangs neglected between his legs. He doesn’t even realise when his hips begin to sway in time, pushing him back to receive Cas’s fingers deeper inside him.</p><p>“Does that feel good, Dean?” Castiel asks quietly, “Remember what I told you, no giving in to it. This is discipline not pleasure.”</p><p>Dean whines in the back of his throat, still wiggling his ass to try and take more of him inside.</p><p>“You seem to be managing this quite well. I think you deserve one more finger, don’t you?”</p><p>Dean nods, hypnotised by the sensations filling his ass, a pressure slowly building from a point deep inside him, an almost frantic heat. He moans as, firmly, Castiel begins to spread his fingers inside him, stretching him open to accept a third finger into his tight hole.</p><p>Castiel pauses, agonizingly, looking down at Dean’s ass spread open on his hand, his cock dripping wetness onto the floor. He’s quivering, his body straining against the need to come, and he indulges him, pushing his third finger into his hole so slowly and gently that Dean can only groan at the fullness.</p><p>The ache inside Dean is almost too much to bear, and he begins to whimper and cry out with every slight movement of Cas’s hand. Carefully Cas inches his fingers in and out, making sure to keep the pace slow, driving Dean towards his inevitable orgasm. When Dean begins to clench his hole, he stops, one hand on the small of his back, the other firm in his ass to hold him still.</p><p>“Dean, I told you, this is a punishment not an indulgence. I can see quite well how close you are to breathing the rules again. So I’m going to take my fingers out now--”</p><p>Dean cries out, mewling helplessly in protest as Cas shushes him.</p><p>“-- and you’re going to turn around, say thank you, and go back to class. Alright. Ready now.”</p><p>Slowly, devastatingly, Cas pulls his fingers out, Dean pleading and whining with every inch, his whole body begging Cas not to do it. As the tips of his fingers leave Dean almost sobs before, legs shaking, he turns around.</p><p>“Th--thank--thank you, sir”, he whispers, lips parted, eyes dazed.</p><p>Cas nods his approval, then holds his shoulder and spanks him again, once on each cheek. He helps Dean pull up his pants, the zip bulging obscenely around his red and weeping cock, lube smeared across his ass making a mess at the back.</p><p>“You’ve been very good, Dean. Very obedient, when you want to be. I feel certain I will be seeing you again soon.”</p><p>With that, Castiel ushers a stumbling, stunned Dean out of the room, the door closing loudly behind him. </p><p>-------------------</p><p>A few minutes pass, Dean just leaning against the wall outside the door, trying to control his breathing as he ruts helplessly against nothing. A quiet breathy moan escapes his lips as he clenches his fists to control the temptation to touch himself. Then, behind him, the door flies open and Cas comes out.</p><p>“Dean?”</p><p>Dean turns to him, burying himself in his lover’s arms, letting out a pathetic desperate sob as he presses the whole length of his body against Cas. Cas holds him tight, stroking through his hair and pressing little kisses to his forehead as Dean slowly gets himself under control.</p><p>“Was that what you wanted?”, Cas whispers into Dean’s hair.</p><p>Dean nods, still shaking a little as he starts coming down from the almost-high Cas gave him.</p><p>“You were so good Dean, so perfect.”</p><p>The praise makes Dean blush again, and he lets Cas pull him across the hall and into their bedroom. Cas curls around him on the bed, just holding him close as he shivers through the aftershocks of the edging, occasional little whimpers and sighs breaking through despite himself. Eventually he calms, looking up at Cas with a shaky smile on his face.</p><p>“We gotta do that again some time Cas. You are really, really good at that.”</p><p>Cas laughs quietly, hands soothing down Dean’s back.</p><p>“Whatever you need, Dean.”</p>
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